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EP0056956B1 - Dérivés de l'indane, leur préparation et leur utilisation - Google Patents

Dérivés de l'indane, leur préparation et leur utilisation Download PDF

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Publication number
EP0056956B1
EP0056956B1 EP82100238A EP82100238A EP0056956B1 EP 0056956 B1 EP0056956 B1 EP 0056956B1 EP 82100238 A EP82100238 A EP 82100238A EP 82100238 A EP82100238 A EP 82100238A EP 0056956 B1 EP0056956 B1 EP 0056956B1
Authority
EP
European Patent Office
Prior art keywords
indanyl
difluorophenoxy
group
amino
indanone
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP82100238A
Other languages
German (de)
English (en)
Other versions
EP0056956A3 (en
EP0056956A2 (fr
Inventor
Eberhard Dr. Schröder
Clemens Dr. Rufer
Irmgard Dr. Böttcher
Joachim-Friedrich Dr. Kapp
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Pharma AG
Original Assignee
Schering AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering AG filed Critical Schering AG
Priority to AT82100238T priority Critical patent/ATE16701T1/de
Publication of EP0056956A2 publication Critical patent/EP0056956A2/fr
Publication of EP0056956A3 publication Critical patent/EP0056956A3/de
Application granted granted Critical
Publication of EP0056956B1 publication Critical patent/EP0056956B1/fr
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors

Definitions

  • the invention relates to new indanyl derivatives according to claim 1, a process for their preparation according to claim 9 and pharmaceutical preparations according to claim 8, which contain these indanyl derivatives as an active ingredient.
  • DAB 7 low-viscosity paraffin
  • test substances are administered orally daily for 4 days from the 11th day of the experiment.
  • the substances are administered as a clear aqueous solution or as a crystal suspension with the addition of Myrj 53 (85 mg%) in isotonic sodium chloride solution.
  • the rats are divided as evenly as possible into different groups with regard to their body weight. After plethysmographic volume measurement of the right hind paw, 0.1 ml of adjuvant is injected into this subplant.
  • the right hind paws are measured from the 14th day of the trial to the end of the trial.
  • the test duration is three weeks.
  • the healing of the animal's right paw is determined as a function of the dose of test substance applied.
  • the following table shows the results of the compounds 3 to 5 according to the invention obtained in this test in comparison with the structurally analogous indanyl derivatives 1 and 2 known from European Patent Application 0 009 554.
  • the results show that the compounds according to the invention are effective at such a low dosage are, in which the comparison substances show practically no effectiveness.
  • the new compounds are therefore suitable in combination with the carriers commonly used in pharmaceutical pharmacy for the treatment of diseases of the rheumatic type (such as osteoarthritis or ankylosing spondalitis), bronchial asthma, hay fever, etc.
  • diseases of the rheumatic type such as osteoarthritis or ankylosing spondalitis
  • bronchial asthma hay fever, etc.
  • imidazole derivatives of the general formula I according to claim 1 are also suitable for the treatment of migraines and dysmenorrhea and reduce the risk of thrombosis.
  • the pharmaceutical specialties are produced in the usual way by converting the active ingredients with suitable additives, carrier substances and flavor correctives into the desired application forms, such as tablets, dragées, capsules, solutions, inhalants, etc.
  • tablets, coated tablets and capsules are particularly suitable which contain, for example, 1 to 250 mg of active ingredient and 50 mg to 2 g of pharmacologically inactive carrier, such as lactose, amylose, talc, gelatin, magnesium stearate and the like, and the usual additives .
  • pharmacologically inactive carrier such as lactose, amylose, talc, gelatin, magnesium stearate and the like, and the usual additives .
  • the starting substance for this synthetic step can be obtained in two ways:

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pulmonology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (9)

1. Dérivés de l'indane de formule générale 1 ci-dessous:
Figure imgb0006
dans laquelle:
RI représente un atome d'hydrogène ou un groupe méthanesulfonyle ou acétyle et
R2 et R3 forment ensemble un groupe oxo ou hydroxy-imino ou bien sont deux atomes d'hydrogène, ou encore R2 est un atome d'hydrogène et R3 un hydroxyle ou un groupe amino, et, si R3 est un groupe amino, les sels de ces dérivés formés avec des acides sans inconvénient physiologique.
2. N-[6-(2,4-Difluorophénoxy)-5-indanyl]-méthanesulfonamide.
3. N-Acétyl-N-[6-(2,4-difluorophénoxy)-5- indanyl]-méthane-sulfonamide.
4. 6-(2,4-Difluorophénoxy)-5-méthylsulfonyl- amino-1-indanone.
5. 5-(N-Acétyl-N-méthylsulfonyl-amino)-6-(2,4-difluorophénoxy)-1-indanone.
6. N-[6-(2,4-Difluorophénoxy)-1-hydroxy-5- indanyl]-méthane-sulfonamide.
7. Chlorhydrate de N-[1-amino-6-(2,4-difluoro- phénoxy)-1-indanyl]-méthane-sulfonamide.
8. Préparations pharmaceutiques caractérisées en ce qu'elles contiennent comme matières actives un ou deux dérivés de l'indane selon l'une quelconque des revendications 1 à 7.
9. Procédé de préparation de dérivés de l'inda- ne selon les revendications 1 à 7, procédé caractérisé en ce que l'on condense, de manière en elle-même connue, un composé de formule générale Il:
Figure imgb0007
dans laquelle
R1, R2 et R3 ont les significations données à la revendication 1, avec le chlorure de l'acide méthane-sulfonique, et le cas échéant on réduit les dérivés dans lesquels R2 et R3 forment un groupe oxo ou un groupe hydroxy-imino, ou an acétyle ceux dans lesquels R1 est un atome d'hydrogène.
EP82100238A 1981-01-27 1982-01-14 Dérivés de l'indane, leur préparation et leur utilisation Expired EP0056956B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT82100238T ATE16701T1 (de) 1981-01-27 1982-01-14 Neue indanyl-derivate, ihre herstellung und verwendung.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3103372 1981-01-27
DE19813103372 DE3103372A1 (de) 1981-01-27 1981-01-27 Neue indanyl-derivate, ihre herstellung und verwendung

Publications (3)

Publication Number Publication Date
EP0056956A2 EP0056956A2 (fr) 1982-08-04
EP0056956A3 EP0056956A3 (en) 1982-11-17
EP0056956B1 true EP0056956B1 (fr) 1985-11-27

Family

ID=6123795

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82100238A Expired EP0056956B1 (fr) 1981-01-27 1982-01-14 Dérivés de l'indane, leur préparation et leur utilisation

Country Status (10)

Country Link
US (1) US4375479A (fr)
EP (1) EP0056956B1 (fr)
JP (1) JPS57176948A (fr)
AT (1) ATE16701T1 (fr)
AU (1) AU555252B2 (fr)
CA (1) CA1175443A (fr)
DE (2) DE3103372A1 (fr)
DK (1) DK155663C (fr)
GB (1) GB2092144A (fr)
IE (1) IE52717B1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3208079A1 (de) * 1982-03-04 1983-09-08 Schering AG, 1000 Berlin und 4709 Bergkamen Neue indanyl-derivate, ihre herstellung und verwendung
US4555406A (en) * 1983-09-06 1985-11-26 Schering Aktiengesellschaft Indanyl derivatives, their preparation and use
DE3343331A1 (de) * 1983-11-28 1985-06-05 Schering AG, 1000 Berlin und 4709 Bergkamen Verfahren zur herstellung von indanyl-derivaten und deren verwendung
US5604260A (en) * 1992-12-11 1997-02-18 Merck Frosst Canada Inc. 5-methanesulfonamido-1-indanones as an inhibitor of cyclooxygenase-2
GB9420616D0 (en) * 1994-10-12 1994-11-30 Merck Sharp & Dohme Method, compositions and use
US5409944A (en) * 1993-03-12 1995-04-25 Merck Frosst Canada, Inc. Alkanesulfonamido-1-indanone derivatives as inhibitors of cyclooxygenase
US5840746A (en) * 1993-06-24 1998-11-24 Merck Frosst Canada, Inc. Use of inhibitors of cyclooxygenase in the treatment of neurodegenerative diseases
AU4479096A (en) * 1995-01-31 1996-08-21 Merck Frosst Canada Inc. 5-methanesulfonamido-3h-isobenzofuran-1-ones as inhibitors of cyclooxygenase-2
US5681842A (en) * 1996-11-08 1997-10-28 Abbott Laboratories Prostaglandin synthase-2 inhibitors
EP1498140A2 (fr) * 1997-04-18 2005-01-19 G.D. Searle & Co. Procédé relatif à l'utilisation d'inhibiteurs de cyclooxygénase-2 dans la prévention des maladies cardiovasculaires
ITMI20010733A1 (it) 2001-04-05 2002-10-05 Recordati Chem Pharm Uso di inibitori dell'isoenzina cox-2 per il trattamento dell'incontinenza urinaria
DE10142659A1 (de) * 2001-08-31 2003-03-20 Aventis Pharma Gmbh Verwendung von mehrfach substituierten Indan-1-ol. Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas
DE10142661B4 (de) * 2001-08-31 2004-06-09 Aventis Pharma Deutschland Gmbh Mehrfach substituierte Indan-1-ol-Systeme und ihre Verwendung als Arzneimittel

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0009554B1 (fr) * 1978-07-27 1983-04-27 Schering Aktiengesellschaft Dérivés de l'indane, procédé pour leur préparation et compositions pharmaceutiques contenantes ces composés

Also Published As

Publication number Publication date
AU7988782A (en) 1982-08-05
US4375479A (en) 1983-03-01
ATE16701T1 (de) 1985-12-15
JPS57176948A (en) 1982-10-30
DK155663C (da) 1989-09-04
DE3103372A1 (de) 1982-09-02
GB2092144A (en) 1982-08-11
DK35882A (da) 1982-07-28
EP0056956A3 (en) 1982-11-17
JPH0150698B2 (fr) 1989-10-31
AU555252B2 (en) 1986-09-18
IE52717B1 (en) 1988-02-03
DK155663B (da) 1989-05-01
EP0056956A2 (fr) 1982-08-04
IE820168L (en) 1982-07-27
CA1175443A (fr) 1984-10-02
DE3267634D1 (en) 1986-01-09

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